


The Wedding Date

by existential1rony



Category: Chicago PD (TV)
Genre: Eventual Romance, F/M, Fluff and Angst, Sexual Tension
Language: English
Status: Completed
Published: 2018-10-24
Updated: 2018-10-24
Packaged: 2019-08-06 18:13:35
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,400
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16392647
Author URL: https://archiveofourown.org/users/existential1rony/pseuds/existential1rony
Summary: Jay asks Hailey to come with him to Will & Natalie's wedding, as friends... or are they? Just a little more Upstead to help get you through.





	The Wedding Date

It’s a couple weeks away until Will and Natalie’s wedding and I still haven’t established my plus-one yet. With everything that’s been going on, it’s just fallen by the wayside. I was going to ask Hailey to come with me a few months ago, it seemed like a no-brainer; but after finding out about her and Adam, and all the tension that ensued, I started to have my doubts. It’s been a month now since all that transpired, and while Hailey and I are now on better terms, we’re still not back to 100%. I mostly blame myself, I got so angry… well, if I’m being honest, jealous. I got jealous. I had just started to accept that I may have been developing feelings for her, and boy, did that throw me for a whammy. I know I had no right, especially since she’s given me no inclination that she may feel the same about me, still, I couldn’t help it. Adam!? Adam! I just didn’t understand it. Thankfully, she swiftly ended things with him once she knew I knew (& a few others.) It was probably all for the best anyway; I shouldn’t have been falling for another partner. Still, I’ve decided today that I am going to ask her to escort me to the wedding despite everything. There’s really no one else I’d rather go with, or feel comfortable around to bring, even if it’s only as friends. As much as I think about all of the above, and tell myself it’s no big deal, I can’t help but feel nervous. In fact, I seem to always have butterflies in my stomach whenever I’m in close proximity with her these days. They’re happening right now, as I glance at her from the corner of my eye from the driver’s side. It’s been a relatively quiet ride and stakeout, and I know it’s time to rip the band-aid.   
“Yes Jay?” I hear Hailey ask, spurring me from my thoughts.   
“I didn’t say anything.”  
“No, but you were thinking it. Your side-eye is burning a hole into my head.”   
“Sorry, you just look so peaceful and serene sipping your coffee, angelic even!”  
“Nice try! What’s really up?” I laugh; she truly knows how to call me on my BS and see through things.   
“Nothing, really. It’s just, it’s almost Will’s wedding soon, and I know how much fun you have with them when we all hang out at Molly’s. And if Molly’s is a fun hangout, it seems like it would be amplified at a big reception and, well…”   
“Jay, are you trying to ask me to come to the wedding? Why are you beating around the bush?”  
“Well, I was getting to that. You know me; I don’t really make the greatest choices, nor have the best luck with women these days. So I was thinking who better to take than my best pal? We all know if anyone can keep me in check if family drama arises, it’s you!”   
She nods her head slightly and then stares out the front window, not saying anything for what feels like forever. I can’t get a gage on what she’s thinking and the butterflies have magnified. Finally, she looks back at me.   
“I don’t know. Do you think it’s a good idea? I mean, under regular circumstances I’d say yes, but with everything that’s happened with us recently… we kind of only just started getting back to normal. Should we really risk potentially rocking the boat again?”   
My disappointment is creeping in, but I power through. “Listen, if this is about Adam, if you guys are still… hanging out… I’m only asking as a friend. But, if you don’t want to go, I’ll understand. I can go stag, or maybe ask Kim or someone.”  
Hailey sighs. She seems to be pondering her next words. “This has nothing to do with Adam. I told you him and I were through, and that it was a meaningless fling. I just… I don’t want to screw anything up with us more than what’s already happened.”   
“It’s fine, no pressure, I’ll figure something else out. I just thought it’d be nice to go with my friend, someone I’d actually enjoy spending the day with.” I turn to look out the window so she can’t see the emotions on my face. About a minute goes by when I feel her grab my hand.   
“I’ll go.”  
“Hailey, you really don’t have to, it’s fine.”  
“I want to!” I give her a questioning look.  
“Really! Besides, it’s about time I get some payback for all the times you’ve drank my whiskey and beer and never replenished.” She gives me her classic Hailey smile as she says that.   
“Ok, great! I promise, you won’t regret it, Halsteads are the best dancers.”  
“Oh, I can’t wait to see you drunkenly cut a rug!”   
We both laugh, genuinely, for what feels like the first time in a while. As I’m about to retaliate, the two-way goes off. As disappointed as I am to have the moment cut short right now, I can’t wipe the grin off my face. I don’t think anything will get me down today. 

. . .

I just finished applying the last layer of lipstick when I start to fold my hands down my dress. I try to tell myself it’s to even out any apparent wrinkles, but really, the motion is helping to calm my nerves. I’m still not sure it was the best idea to agree to go with Jay tonight. Not that I don’t enjoy spending time with him, in fact, I enjoy it probably too much, which is the problem. It was bad enough I got myself into the mess with Adam, trying like Hell to push aside any feelings I had for Jay. Then of course he had to go and find out, and things got even more complicated from there. My stupid, idiot partner had to go and get shot and it unlocked all the emotions I had been blocking. Naturally, right when we’re getting back to normal, less tension and just regular partners again, he goes and asks me to his brother’s wedding! I wanted to say no, if only to salvage my heart from being in a romantic setting with Jay, but that would be more suspicious. It makes sense he’d ask me as a friend, the old me would have never hesitated to say yes. The door bell suddenly rings, pulling me from my thoughts.   
I run over to answer it and just as I pull the door back, Jay’s mouth drops open. Oh God, he looks so good in a tux. This is bad, this is very bad.  
“WOW Hailey, you look Amazing!” I hear him say, pulling me out of my haze.   
“Thanks! You don’t look too bad yourself.”   
“Here, I got you this. I wanted to bring you something for coming with me, it means a lot. I know we haven’t been at our best recently.”   
He hands me a single, beautiful red rose. What is he trying to do to me!? Augh, breathe Hailey, breathe.   
“Oh, thank you, it’s beautiful! You didn’t have to do that.”   
He shrugs like it was nothing and walks into the hallway.   
“You almost ready? I think I have to be there a little earlier now, sorry, best man duties apparently.”   
“Yup, just let me put this in a vase and grab my purse.”   
I run into the kitchen and start fiddling with my dress again. If I thought I had nerves before he got here, they’ve quadrupled. Well, it’s now or never. You can get through this; you’re a badass cop who deals with things most people would never believe. I keep repeating this in my head as I walk back over to Jay.   
“Ok, let’s do this. First round’s on me, but you got tip.”  
“Haha, it’s a deal. That open bar will never know what hit it!”   
I smile as Jay and I walk outside. This is good, this will be good. 

. . .

The first hour or so went by pretty uneventfully. I haven’t spent a lot of time with Jay yet, since he’s in the wedding, he’s been pretty busy running around taking pictures and doing all those kinds of duties. He ran over to me a few minutes ago again to make sure I was doing okay.   
“I’m so sorry, I hope you’re doing alright. I hope the bar and cocktail hour has been good. I promise once I get through this speech, I won’t leave you alone again.”   
“It’s fine Jay, really. It’s not like I don’t know anyone here.”   
The truth is, while I do know quite a few people through all the departments, I was never the best at mingling or making small talk. It’s just not me to open up to those I don’t really know. Outside of saying hello to some, I’ve mostly kept to myself. Which has given me a good head start on the bar, and it’s done wonders for calming my insides.   
Right before the speeches start, April makes her way over to our table.   
“Hey Hailey, how are you? You look great in that dress!”  
“Thanks, April. You look beautiful as well! It must be great for all of you guys to have a night away from the hospital.”  
“Yes, we’ve definitely been taking advantage, that’s for sure.” She clinks her glass to mine.   
“Jay looks super handsome tonight!” she nods up at him sitting on the stage with Will, Natalie, and the rest of the wedding party.   
“He does, he really does.” I honestly mean it, he’s by far the best looking guy in the room.   
“Are you two, y’know, an item now?”   
“Oh no, our partnership has been kept strictly platonic. I think we’ve both gone down that road before, it never works.”  
“Hmm, that’s too bad. Will is always telling me all the nice things Jay raves about you.”  
I blush at her words, but do my best to downplay the situation. “Really? Well, that’s sweet of him, we’re good friends.”   
“If you say so… Looks like they’re officially kicking off this party soon, I should get back to my seat. I’ll catch you on the dance floor later, I hope.”  
“Yes, definitely. Nice seeing you!” She starts to walk away right as the maid-of-honor begins her speech. As much as I like April, I’m glad that ended up being short and sweet. I’m sure she’s the first of many who will question if we’re a couple tonight, but I’d rather not think about it. I can’t help but wonder what Jay says about me, though. From my understanding, him and Will have never been overly close. I’m still pondering all these thoughts when Jay takes the mic to speak. As I listen to him, I can’t help but be captivated. I really am in trouble. He’s doing a great job, and wrapping up, when the ending of his speech really hits me.   
“…and I just think they’re the perfect example because they developed trust before they were ever together. They were always there for each other, they always had each other’s backs, they made each other laugh, and really, what more could you need to start a base of love off of? I’ve loved watching them grow together. I’ve never seen Will look at another girl like he does Natalie, and that’s really special and rare. So please, raise a glass with me, to Will & Natalie…”   
I raise my glass with a tear in my eye. The second after everyone takes a sip, I pound it down, not knowing how else to keep my emotions locked up at this point. 

. . .

I’ve never been so excited to be done with responsibilities and finally get back to Hailey. I feel so bad I had to leave her for as long as I did, especially since she’s doing this favor for me. As I walk closer to her, I feel the butterflies start to form again, she really does look gorgeous tonight. I notice that she seems a little upset and my heart breaks. I walk up to her and place my hand on her shoulder, seemingly stirring her from her thoughts.   
“Hailey, is everything ok? I’m so sorry that all took so long.”   
“I’m fine… I just really loved your speech. Who knew you had it in you, or that I’m such a sap? I hardly know Will & Natalie… but I feel like I do.”   
“You really liked it? You know I’m not the best with those things, the words kind of flew out of me from somewhere.”   
“It was great! C’mon, let’s go do a shot, you have a lot of catching up to do!”   
She grabs my hand and yanks me to the bar. Who am I to turn down a beautiful girl leading me to free booze!?   
The hours are ticking by, and I’m kind of sad because I’m having a great time with Hailey. I’m really happy I still asked her, despite occasional awkwardness, I really can’t think of anyone else I’d want here. We’ve spent at least two hours just talking and laughing, while we eat and drink.   
“…I still can’t get over the look on your face when you were like, ‘Freeze Jerk!’ and he dropped his bag of ice cream and eggs so fast!” Hailey laughs hysterically as she mimics me.  
“Me? It was your CI who said the perp might be transporting the goods in a grocery bag. I swear, I still think you two purposely punk’d me.”  
“We most certainly did not, it’s not my fault you were testy that day and wanted to pin anyone doing some food shopping!”  
“Yea, sure… ‘Oh Jay, look, over there, I think that guy matches our description. Please, go get him, I haven’t finished my coffee yet.’”  
“I do NOT sound like that! And I HADN’T finished my coffee yet… you had already gotten to eat a bagel and a donut, it was only fair.”   
“Some partner you are, taking a picture as the poor guy almost pissed himself and I got egg guts splattered all over my shoes.”  
“It’s yolk, Jay, and I offered to help you clean them.”  
“Yea, after two hours of you hysterically laughing and telling everyone else who would listen!”  
“Oh, get over it grumpy. C’mon, you promised me you’d show me your drunken jig.”   
She grabs my hand and yanks me up as she starts pulling me to the dance floor. The second I stand, I know I’m tipsy, and Hailey is right there with me. I swear, I haven’t had this much fun in… ever!   
“I did not promise you a jig, I promised you some mild dancing.”   
“Oh, don’t worry Jay, by the end of the night I’ll have you jigging all over the place!”  
I raise my eyebrow at her and smirk. She rolls her eyes at me.   
“Let’s go pervert, keep it moving.” She gives me a slight shove to the middle of the floor.   
We start rocking out to some Bon Jovi song, raising our fists jubilantly. Hailey jokingly does her best impression of an air guitar, and I crack up. She really never ceases to amaze me. The song switches to some current EDM music I don’t recognize and we continue on with our goofy dancing. I grab her and twirl her at one particular beat, and when I bring her back into my chest, she has a strange look on her face and quickly pulls back. I think I screwed up, but as quickly as her mood changed, she switched back instantly into dancing mode. Phew! We continue on for another couple songs, when a slow one starts to play. I hesitate for a bit, then put out my hand to her. What’s the worst that can happen? We’re already on the floor.   
She seems to hesitate briefly as well, but eventually takes my hand. We quietly start to slow dance. My one hand on her hip, hers resting on my shoulder, our other hands entwined. We leave plenty of space between us, but I feel like I’m right on top of her. My heart is beating so fast. It’s then I look over and see April dancing with her date, giving a nod and knowing look to Hailey. She appears to blush and turns away.   
“What’s that about?” I ask Hailey.   
“No idea. She must just be saying hi to us.”   
The song continues and we get quiet again, when suddenly Hailey speaks up.   
“Y’know, this is probably the first time I’ve ever really slow danced.”   
“What!? How is that possible? What about school dances and other weddings?”   
“I don’t know, it just is. I dumped my high school boyfriend right before Prom because I caught him cheating on me. And somehow, any other wedding I’ve been to, I wasn’t in a serious relationship at the time. So, unless you count my dad or brothers, this is it.”   
She looks up at me wide-eyed. I can tell she’s not depressed over this fact, but definitely in shock she just gave me all that info. I feel honored and pull her closer. It’s definitely the alcohol at this point because I suddenly whisper into her ear.  
“Well, I’m glad I can be your first.” I pull my face back, ready for her to deck me if it comes down to it, but luckily she’s chuckling and shaking her head.   
“Idiot!” She says as she pulls my hair at the base of my neck, right as the song switches back to a faster one.   
“Ow!” I yelp as I twirl her again. She laughs hysterically and my heart feels full. I’m totally screwed, but what a great night it’s been to realize it. 

. . .

As we’re pulling up to my house, I’m actually really sad to see the night end. I had a great time, as I always do with Jay, but this was probably the first time since the Adam ordeal that there was no real awkwardness. Which makes me glad because I hated being at odds with Jay. He seemed to really enjoy the night too. He pays the driver and we walk up the steps to my house. Once inside, I take off his suit jacket and hand it back to him. A gesture that warmed my heart, and upper body, as we left the wedding.   
“Thanks again for letting me borrow it, it was really sweet of you.” He drapes it on a stool in the kitchen as he grabs two glasses out of the cabinet.   
“It was my pleasure. Thank you for coming with me, we made an awesome pair if I do say so myself.” He grabs the whiskey out of another cabinet and starts to pour.   
“Help yourself, Jay!”   
“Oh, did you not want any?” He raises his brow and starts to put it back after pouring only the one. I grab the glass that’s already full.   
“Thanks, don’t mind if I do!”  
“Classless and shameless, Hailey.” He then pours his and we both laugh and lean over the kitchen island as we talk.   
“I know I’ve said this ten times already, but thanks again. I had a really great time tonight, and I just don’t think I would have if it was anyone else there. No one I’d rather want as my partner!”  
I know he means it as a compliment, and I’m happy tonight made him so happy, but I can’t help the little part of me that feels disappointed that he called me, “partner.” This is good, this is what I wanted, keep the feelings buried and don’t think beyond the partnership. So, why am I so upset?  
“Hailey, are you ok? You got a little quiet.”   
“Sorry, yea I’m good, was just thinking over the night. You made an excellent date and were a proper gentleman. I had a lot of fun.”  
“I try, I mean, I’m no Ruzek or Atw…” He stops himself, obviously realizing what he said. “I’m sorry, I didn’t mean… I’m not trying to rehash that.”  
“It’s ok Jay, I know. As long as you know the Adam thing was a mistake. We went over this many times. I was vulnerable and it just happened…”   
“It’s fine Hailey, really. I’m not angry anymore, it’s not my place anyway.” He covers my hands with his on the counter and nods his head to assure me. We end up staying like that a beat too long and both pull away quickly after realizing. Jay pulls out his wallet and shakes some coins out of it. I look at him suspiciously.   
“C’mon, we’ve been drinking all night, what better game to play than Quarters?” He grabs another glass from the cabinet.  
“Seriously? I haven’t played this since college. I’m gonna be terrible.”  
“Well, I was going to suggest Beer Pong, but I figured you were probably limited on the solo cups, balls, and beer.”   
“You would be correct there. Fine, let’s give it a go, but don’t judge me if I suck.”   
Jay grabs his heart and looks aghast. “Hailey, I would never judge if you suck. No girl should get judged for that!”  
I throw a quarter at his chest and shake my head. “Let’s go, smartass! Ladies first.” I hand him a quarter and wink at him.  
“Oh, it’s on!” He bounces the quarter off the counter and misses the glass completely.   
I take one and follow suit, only mine actually goes in the cup. He sips his whiskey and raises his brow at me. We continue on for about 10 minutes, and in that span, I’ve gotten about 15 quarters in the glass to his 1.   
“You’re cheating!”  
“I am not! How would I even begin to cheat at this game? And they’re your quarters!”  
“It’s your glass!”  
“Really? That’s what you’re going with? Not the fact that you stink? “  
“Halsteads don’t stink at anything.”  
“The empty cup begs to differ.” I nod my head at him sympathetically.   
He grabs the quarters and puts them in his fist.   
“Hey, it’s my turn, give them back.”  
“I don’t think so, Hailey.”   
“Aww, is poor wittle Jay a sore loser?” I tease him as I try to pry a quarter from his fist  
“You will never get these quarters back.” He smiles and clenches his fist tighter.   
I try yanking open his hand with both of mine. No such luck. He raises his hand above his head, knowing I’m too short to reach.   
“Really Jay? What are we, five?” I stand on my tiptoes trying to pull his hand down. It’s pointless.   
I don’t know what comes over me. Chalk it up to all the alcohol and the repressed feelings because I’d never be foolish enough to do it otherwise, but here we are. I lean closer and nuzzle my face into Jay’s jaw. I feel him swallow, so I go in for the kill. I nip Jay’s earlobe with my tongue and teeth and give it a tug. He shivers as he drops the quarters to the floor. Success. Right as I’m about to lean down to pick one up, he grabs me by my arms and pushes me against the wall. Before I can register what’s happening, he’s kissing me. Oh boy, this is trouble. I’m in trouble. Shit, what was I thinking? Oh, fuck it! I wrap my arms around his neck and kiss him back. The moment intensifies and seems to continue on forever when Jay begrudgingly pulls away. His eyes are glazed over from being turned on, which slowly starts looking like regret.  
“I’m sorry, Hailey. I didn’t mean to take advantage…”  
Great, he regrets it. Of course he regrets it. We’re partners. Reason #23 on why having feelings for him is a bad idea. I’m so stupid.   
“You didn’t take advantage Jay, I practically forced you…”  
“Not that I didn’t want to do it, or it wasn’t the greatest kiss ever…”  
We speak over each other at the same time. Wait, did he just call it the ‘greatest kiss ever’?  
“But, I know we had a lot to drink and you think of me only as your partner.”  
“Jay, you’re not just a partner to me. You’re way more than that… but maybe it’s not the best idea. Maybe we should discuss this all when we’re more sober.”   
“No, yea, you’re right. I’ll help you clean this up then get an Uber.” He bends down to start picking up the quarters and I lean down with him. “Besides, I always screw up relationships anyway, and since you’re the most amazing person I know, I don’t want to jeopardize that.” He looks at me with the sweetest and saddest eyes as he says that.  
“Fuck it!” Hmm, I think I say that one out loud this time as I grab his cheeks and pull him toward me. I kiss him with all I have. It doesn’t take him long to reciprocate it. Before I know it, Jay’s lifting me up and carrying me to my room. Once I hit the bed, I pull him down on top of me. There’s not much talking after that; which is fine, we can totally talk later… much later. 

. . .

The sun in my eyes is strong enough to make me squint awake. I feel muscular arms holding me close and a body spooning me, when everything from last night comes flooding back. Jay. I freeze for a second and debate getting out of bed, in fear he’s going to wake up and regret it. We were both pretty drunk. He must sense that I’m awake because his arms get tighter around me.   
“Don’t even think about it!” I hear him say.   
I smile into the pillow. “What, you mean you’re not gonna run for the hills now that we’re sober again?”  
He kisses my hair and in a groggy voice responds, “There’s no place I’d rather be, ever again.”   
I wrap my arms over his. “Fine, but you’re making the coffee.”  
“Deal!”   
Who says this can’t work? It only has to work once. The idiot just better not get shot again, he’ll really have to answer to me now. I snuggle into him and fall back asleep. It’s the most peaceful sleep I’ve had in a while.

**Author's Note:**

> [A/N: Just kind of threw this one together and pulled it out of my butt. Hope you enjoy it. Thanks for all the positive vibes! Wanted to get some more Upstead out there ASAP. I hope they rectify their relationship soon.]


End file.
